Pep Guardiola's Manchester City had just 37.8 per cent of possession at Molineux as their title hopes suffered another blow.
Manchester City suffered another hammer blow in their bid to keep the Premier League title race alive with a 3-2 defeat to Wolves, making unwanted history for Pep Guardiola in the process.
City missed the chance to close the gap to leaders Liverpool to 11 points as Guardiola's side, reduced to 10 men following Ederson's dismissal after 12 minutes, threw away a 2-0 lead.
The defending champions had only 37.8 per cent of possession at Molineux – the lowest recorded by a Guardiola-led side in top-flight history.
Wolves' thrilling win also saw them become just the second team to do the league double over City since Guardiola took over in 2016, with Antonio Conte's Chelsea the only other outfit to achieve the feat in the Catalan's first season in charge.
Additionally, it was Wolves' first double over City since the 1999-2000 campaign, when both were in the second tier, and their first in the top tier since 1960-61.
With Wolves now serious contenders for a top-four finish, City have a fight on their hands just to finish as runners-up.